ethyl 3-fluorobenzoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:80.01; pressure:0.00; stir:

反応条件: temp:80.01; pressure:0.00; stir:

反応条件: temp:60.01; pressure:0.00; stir:

反応条件: temp:50.01; pressure:0.00; stir:

反応条件: temp:50.01; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 mL of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 3-Fluoro-benzoic acid ethyl ester, the reaction mixture was heated at 100° C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(2-Fluoro-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (0.56 g, 2.1 mmol) as brown solid in 14% yield. The solution was cooled to room temperature The organic layer was collected dried over MgSO4(s) concentrated under reduced pressure The resultant precipitate was collected recrystallized from ethanol

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 mL of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 3-Fluoro-benzoic acid ethyl ester, the reaction mixture was heated at 100° C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(4-Fluoro-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (0.56 g, 2.1 mmol) as brown solid in 14% yield. The solution was cooled to room temperature The organic layer was collected dried over MgSO4(s) concentrated under reduced pressure The resultant precipitate was collected recrystallized from ethanol

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 mL of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 3-Fluoro-benzoic acid ethyl ester, the reaction mixture was heated at 100° C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(4-Fluoro-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (0.56 g, 2.1 mmol) as brown solid in 14% yield. The solution was cooled to room temperature The organic layer was collected dried over MgSO4(s) concentrated under reduced pressure The resultant precipitate was collected recrystallized from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: s-Butyllithium (52 mL, 1.4 M in pentane, 72 mmol) was added at −78 C over 90 min. to a solution of p-Anisic acid (5 g, 33 mmol) and TMEDA (11 ml, 72 mmol) in THF (80 mL). After stirring for 15 min. ethyl 3-fluorobenzoate (5 mL, 40 mmol) was added in one portion. The reaction mixture was stirred for 15 min. then it was quenched with water (20 mL). The reaction mixture was then warmed to room temperature poured into water (1.5 L) 1N NaOH (30 ml) was added and the reaction mixture was then extracted with EtOAc. The extracts were discarded. The aqueous phase was then acidified with conc. HCl to pH 1 and extracted with EtOAc. Drying (Na2SO4) and concentration gave a residue which was recrystallized from hexanes/EtOAc to give the title compound as a white solid. was added in one portion it was quenched with water (20 mL) poured into water (1.5 L) 1N NaOH (30 ml) was added the reaction mixture was then extracted with EtOAc extracted with EtOAc Drying (Na2SO4) and concentration gave a residue which was recrystallized from hexanes/EtOAc

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: s-Butyllithium (52 mL, 1.4 M in pentane, 72 mmol) was added at −78 C over 90 min. to a solution of p-Anisic acid (5 g, 33 mmol) and TMEDA (11 ml, 72 mmol) in THF (80 mL). After stirring for 15 min. ethyl 3-fluorobenzoate (5 mL, 40 mmol) was added in one portion. The reaction mixture was stirred for 15 min. then it was quenched with water (20 mL). The reaction mixture was then warmed to room temperature poured into water (1.5 L) 1N NaOH (30 ml) was added and the reaction mixture was then extracted with EtOAc. The extracts were discarded. The aqueous phase was then acidified with conc. HCl to pH 1 and extracted with EtOAc. Drying (Na2SO4) and concentration gave a residue which was recrystallized from hexanes/EtOAc to give the title compound as a white solid. was added in one portion it was quenched with water (20 mL) poured into water (1.5 L) 1N NaOH (30 ml) was added the reaction mixture was then extracted with EtOAc extracted with EtOAc Drying (Na2SO4) and concentration gave a residue which was recrystallized from hexanes/EtOAc